August 26, 2026

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You can spend a million dollars on event Wi-Fi, replace every router in the building, and still watch an entire room of laptops suddenly decide they live in Germany. Because apparently, even the most sophisticated event technology is only one mysterious firmware update away from complete mayhem.
Jen Santos sits down with Josh Shepherd, VP of AI Solutions at Amego, to talk about the event technology failures that make planners twitch. Things like unreliable internet, overcrowded expo floors, broken badge printers, and integrations that become useless the moment Wi-Fi disappears.
What starts as a story about taking over a venue’s entire internet infrastructure turns into a practical conversation about offline-first technology, backup systems, attendee experience, and knowing when the best solution is simply to let everyone into the keynote, badge or no badge.
Josh and Jen are quick to agree blame is useless during an event crisis, calm problem-solving earns client trust, and nobody—regardless of title—is ever too important to carry a box.
Top Takeaways from Josh & Jen’s convo:
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VP AI Solutions, Amego
Josh Shepherd is a global event technology leader with over 25 years of experience spanning agency leadership, enterprise operations, and technology innovation. During his years as Head of Global Event Technology & Innovation at Atlassian, he oversaw the digital infrastructure and strategy for a diverse portfolio of hundreds of events, ranging from intimate regional programs to Tier 1 global conferences. Today, Josh focuses on the intersection of event infrastructure and AI, helping organizations move beyond reactive tools toward proactive guidance systems. Having supported technical elements of programs for organizations such as Google, Nvidia, and Dell Technologies, he is known for a "practitioner-led" approach that balances high-level strategy with the reality of event execution. Josh is a leading advocate for the AI Concierge model, a framework designed to bridge the attendee discovery gap and maximize event value through intelligent, push-based delivery.
Josh: And so everything had an internal cache with a time zone and time setting of Germany. So for some reason, they were broadcasting out a system time of that. So we had whole rooms and swaths of the event where everybody's laptop was switching to 9 hours, 7 hours off local.
Jen: Hey everyone, I'm Jen Santos, and this is Mayhem and Method, where event pros tell the real story of what happened and what it reveals about how events actually work. Hey there, and welcome back to another episode of Mayhem and Method. Today I am here with Josh Shepherd, who is the VP of AI Solutions at Amego. Josh, thank you so much for taking the time to be here today with me.
Josh: Absolutely happy to be here, Jen. It's a lot of fun.
Jen: Yeah. So what is one of your favorite venues to work and why?
Josh: That's, um, yeah, that's a question I'm not prepared for. Okay, what is the Favorite venues. When you sort of, you've been in like what, every major convention center across the country and around lots around the world too, that the ones that are special, they're the ones that are like personal, unique. It's the experience there, the networking, those memories that make it special. So I would say one of my favorite ones was the Fairmont Château Lake Louise. It's in Alberta, Canada.
Jen: Oh.
Josh: And it's in the middle of the Rocky Mountains.
Jen: Yeah.
Josh: And we did an SKO there, a sales kickoff there for a team that was out of South America and they had never seen snow. And this was like a magical kingdom hotel in the middle of 8 feet of snow. And we gave out long johns, those long underwear for the giveaway at registration because it was cold. you know, people had never seen. They didn't, you know, with the trapdoor on the butt, like the real authentic thing, and nobody had ever seen it. In fact, we were getting questions of, does this go under or over my suit?
Jen: Right, right.
Josh: Which of course we said over, absolutely over. But it was so much fun. But yeah, magical moments that are, uh, that you remember, right?
Jen: That is incredible. Yeah, well, great. I'm in Brazil and my husband's Brazilian and we live like basically at the tropics. And so when I took him up to Wisconsin to find my family the first time, and it was for either Thanksgiving, I think it was Christmas actually that year. And so we're sitting there and all of a sudden my brother nudges me and he's like, it's snowing, right? And so I tap my husband and I'm like, it's snowing, neve, right? Portuguese word for snow. And he gets up and it's like 11 o'clock at night and it's pitch dark. And so he just stands there like literally at the picture window for like an hour. And he's just watching it come in. And then of course it accumulates to the point where we could actually go and do something with it. So now it's midnight and he's like, can we go out in the snow? I'm like, well, we can, but you're gonna be extremely unhappy about it. And so now when he goes with me, he puts on like literally like 3 pairs of pants. He's got like long johns and then he puts on like a pair of my running tights underneath it and then he puts on his regular pants. Yeah, it's ridiculous.
Josh: Well, I tell you, living in Canada, Um, the novelty wears off a bit.
Jen: Yes.
Josh: Through the, the 4 or 5 months of winter, but then, you know, spring comes and you forget.
Jen: Totally, totally. Yeah, as a Wisconsin girl, I totally feel that. Absolutely. So now let's get into the meat of the conversation. And so what I want you to do is I want you to tell like a disaster or a mayhem story, if you will, of something that went sideways on site, right? Because we all know that when things go sideways on site, it's almost never Something that actually happened on site that led to it, right? There's going to be like 18 things that happened prior to this that led to everything going sideways on site, or whatever it was that went sideways. And so after you kind of tell your story for a couple of minutes, we'll stop, and I like to talk about what happened before what happened happened. Basically, what were the precursors that led to this condition on site that led to this odd experience? And now I hand it over to you.
Josh: Thanks. You know, I was saying that I've been a part of technology, event technology, on like every element of an event beginning to end through my career at some point. And we've done small high-touch like executive events to huge tier 1 B2B events around the world. And honestly, it's still the same. It's these little things that you remember that almost derail the event. And it's those little things and the solving of them that gives us all as planners the trauma bond that we can relate to each other about. So, I was thinking about this question and I think I'm gonna talk about internet because it's something that I think everyone will relate to.
Jen: Yes.
Josh: And I think the stories are endless of internet at venues just makes everybody sort of curl up and twinge a little bit. And so, I'll give you an example. The one is that I was planning a big flagship event in a major event city And the internet was very poor at the facility the one year. So, the next year, we decided to go with a vendor and replace it and do an internet takeover, not use the venues. And we brought in an elaborate plan with truckloads of equipment and access points and routers and wire. And we restrung the convention space and basically blanketed it ourselves. And actually, aside, I got to look as part of this into the server room that the hotel and convention center had, and it was their server rack, and it was all fiber optic cable, all one color, and it literally looked like a bird nest.
Jen: Oh.
Josh: Like it was just a ball of yarn. And I thought, how on earth could somebody ever troubleshoot this? And you think they're running—
Jen: Right.
Josh: billion-dollar-a-year enterprise on this craziness. And how good would a co-op student with a bag of zip ties improve this? But anyway, so we replaced that. We put our server rack in there, we plugged into the fiber, we built it all. And then, well, it generally worked pretty well. Like everything seemed to go well. Internet is one of those things like electricity. It has to work every second, every instant. or people complain.
Jen: Yep.
Josh: So it was a constant— because we did this, it hadn't been fully stress tested, and it was a constant run of small mini emergency issues. Overall, big picture, worked pretty well. But we would learn about something, request support, calm the caller or speaker, whoever it was, you know, go confirm it was reported. They wanted somebody there immediately. report it to leadership because it was always escalated, and then, you know, follow up. And then by the time you were done, there were 10 more waiting for you. So like a couple of consistent problems that kept recurring for us with things like router stickiness, that people would say there's no signal. Well, that's because you're standing beside an access point, you're saying there's no signal, it's because your phone or device is connected to an access point halfway down the hall.
Jen: Right.
Josh: And it didn't jump over. So that was a big thing. And the other crazy thing was we had a ton of the hardware had last been used or manufactured or whatever in, I think it was Germany. And that was the last time. So everything had an internal cache with a time zone and time setting of Germany.
Jen: Oh.
Josh: So for some reason, they were broadcasting out a system time of that. So we had whole rooms and swaths of the event where everybody's laptop was switching to 9 hours, 7 hours off local.
Jen: Yeah.
Josh: And of course, how the heck do you trans— like, how is this happening? Like, um, and of course it was in a hands-on lab for developers, which broke everything on the labs, you know. And by the time we, we finally learned and corrected it, it was, it was just insane, right? And, and totally unforeseen things that the, that the vendor just hadn't, hadn't even considered, right? And I would say the internet is such a crazy thing. about how we think of it in North America. Like the newest installations that blanket spaces are quite good and feature-rich because that's 'cause they're brand new.
Jen: Right.
Josh: And they use the latest in technology, but it could cost you $1 million quite easily, $1 million for a 3-day event to get internet for like 5,000 people. And, you know, it's another thing running events outside North America, you often get the same amount of internet coverage for like 50 grand, where they're just paying for worker time and technicians to drop things because they think about it differently.
Jen: Yeah.
Josh: Like overseas, you're thinking internet's like water. It's coming into the building. Why wouldn't you get it?
Jen: Right.
Josh: Where here, it's like sort of every piece. So it's crazy how much it costs, how much we depend on it. And if something goes down, so we actually started, doing our own backups because event planners, backups on backups, that's what we do.
Jen: Mm-hmm.
Josh: And we started buying our own routers and bringing them with us for critical elements like, think registration, main stage, those couple things. And we found routers that could take hotel internet, conference Wi-Fi, 2 or 3 or 4 SIM cards from different providers, plug them all in, and it would load balance between all those different internet sources. And then automatically, if one dropped, it didn't care. You didn't notice. It just went to the other one. So we started bringing those even on top of the very best internet to try and ensure and as to create another layer. But anyway, there's lots on that topic. That's my critical issue.
Jen: Yeah, no, internet is really, really a big thing. And it, Got me thinking about one time when I was working on a flagship event, and that this was one of those same types of organizations, right? This is a big, like, 20,000-ish person event covering one of the major convention centers. They bring, they bring a team in and they run all their own stuff, right? But it turned out that the routers they had were brand new routers. And it wasn't the time zone thing, although I have heard of that, but apparently there was a firmware bug. They were literally brand new routers that have never been tested. And like by the middle of day 1, like internet was just like not stable the entire week. And this is a developer event. Really, really, really bad event. And then I also remember, this is the other thing, right, is like expo floors. And even if you have really good internet, it almost doesn't matter when you're on an expo floor because as one of my old clients, one of my former clients used to say, He's like, Jen, he's like, bodies are like 80% water and Wi-Fi doesn't travel through bodies. So as soon as you end up with a really congested Exospace, even if all the testing looks really good on the walkthroughs and it might be really great at like 50% capacity, as soon as you start your welcome reception and as soon as you get to your lunch hours where you've got like 70% of attendees down there, it just doesn't work. Right? It just doesn't work. You have a super congested area or you have a really popular activation, you're just, you're going to struggle with your internet and there's no ifs, ands, or buts about that.
Josh: Well, you start getting, like you said, an expo floor, right? So say you have a blanket of APs in a grid or a mesh above the floor space, you bring in 1,000 people, they all are connecting to that.
Jen: Yep.
Josh: Uh, the sponsors don't think that their internet is good enough, so they bring like wireless mobile hubs and things like that.
Jen: Yep.
Josh: Every person coming into that room has at least one mobile device which is transmitting.
Jen: Yeah.
Josh: And so the traffic, the, the, in that room, like the channel space for connecting devices is, it's just insane. So the only way to get through that is, is enterprise-grade hardware. Um, like, that's the only way to deal with that kind of congestion. But yeah, you're right, it's, it's absolutely crazy. And if, if one person's scanner doesn't work once, or somebody's demo doesn't work, then, then, you know, they're screaming that the— that there is a fire alarm and we have to deal with this, right? Like, it is the most important thing to them at that moment because they're there for one thing, which is, which is brand and leads, right?
Jen: Yep, absolutely. Yeah. And even if scanners— like, scanners will If you're using what I believe is a proper type of scanner, right, it's gonna store that information locally on the device and you can just sync it up at the end of the day and everything's fine. Sponsor may have a little bit of panic because the leads aren't updating in real time, but at least it's explainable. But like, if you're running something like, I've done games that have relied on scanning, right? Like if you have a gamification element that relies on scanning and if your scanners aren't syncing, now you have nonstop attendee escalations because, I swear to God, I stopped by that booth. But, but the game is broken. And I'm like, the game isn't broken. Let me send somebody over to sync the scanner again, right?
Josh: Well, it's funny because, you know, in a world where we're putting people on, on the moon, maybe sending them to Mars, you know, we have robots walking around, AI is doing everything that we're doing and, and more, and, and we can't get internet. Um, so the, the solution is like, I've had a lot of people tell me that internet is now stable in this day and age, so don't just assume it's going to be fine. And I'm like, it's such a crazy thing to say.
Jen: Yeah.
Josh: So the trick is to plan for when it— just like what you were saying with the scanners, is you plan for things not to work on the internet. So if you're using like, say, your mobile app or something and the attendees are relying on that to get around, and that's part of the attendee experience funnel is this mobile app, you need to make sure that everything works offline, that there doesn't— because even if it's a moment where they're in a crowded area or they're in a, you know, the depths of a convention center that they don't get some sort of signal, that screws up or it creates friction and a road bump in that, in that person's attendee experience. So, you know, having those backups that everything will continue to work as you expect, that they don't even notice And it's interesting, we've run— one of the things we're— that's something I do a lot of is make sure that our tools and our company make sure that everything works offline. And we had a big major flagship event that was— there was like 8,000 people there or something. I can't remember the number, but their internet, it was a tech company, like a tech enterprise, and it went down in the middle of the event for a long time.
Jen: Oh, man.
Josh: No one noticed. Like, no, we had zero reports of anything. Nobody came and said, I don't know where I'm going. I don't know, because everything just worked offline. And when it came back up, everything updated and continued on as normal. But I mean, that's a testament to, yeah, that importance of having those backup plans like that.
Jen: Yeah. Yeah. I mean, Josh, as you know, I do a lot of mobile apps, right? I do mobile apps for some very, very large trade shows. And when you talk about a giant trade show, they don't necessarily have the resources to go and put in, like, like run their own Wi-Fi, right?
Josh: Mm-hmm.
Jen: So you're talking about trying to run on venue Wi-Fi, and then when you're talking about a large quantity of people, the Wi-Fi, like you just said a couple minutes ago, isn't going to be sufficient to support that quantity of people. And so that's another thing that I do with all of my projects. It's like, okay, like, yep, it needs to be able to support offline mode. Like I've got, we work with, um, of like a blue dot mapping provider now to do like blue dot, like Google Maps type navigation indoors, like between session rooms and everything. And the rule is it has to work offline, right? Our mobile apps have to work offline. And every time, particularly with this one client of mine, if we're going and we're looking at— sorry, I heard the dog and now I'm like, ooh, there's a puppy.
Josh: You know, having a great big dog is great, but when every time somebody walks by the house, it starts barking and I can't make it stop. mute the dog for a couple of minutes.
Jen: No, you totally get it. Anyway, um, what I'm saying is every time we go and we talk to a new integration partner, I'm like, well, is this gonna be able to work offline? And like, it cuts out like 9 outta the 10 integration conversations that I can possibly have with them because so many of these, it's like, oh, we can do a web view. And I'm like, yeah, but that relies on online connectivity and that's not gonna be a thing, you know? And so it really is when you start thinking about internet, and the importance of internet and all the integrations and the pieces of technology you're going to have, it is super, super important, like scanners being available online. What do you do at registration if your internet chokes, right? Like what sort of load balancing, what sort of backup systems can you have in place? Can you keep literally a server in your back pocket so you can pop it out at any moment?
Josh: So one of the things I was going to tell— talk about today was badges, and we've— I've done that before, but I think it's been overdone a little bit that Everybody's got a trauma story about badges, right? No?
Jen: They do, but we always, we're always here for another one, so let's go for it.
Josh: Right.
Jen: Yes.
Josh: So, um, yeah, I, I've been at an event probably 10 years ago, and there was a event badge printing— was different technology then, but we had something update overnight, like Chrome or something pushed an update, broke the printing mechanism. I got pulled off site at like 2 AM to go to another event. And so the team that was left there was trying to check in 1,000 people in 5 minutes before the keynote started because that's when they showed up. And it was just the panic. And I think then they were on the phone to me saying, how do I fix this? And I think part of the event planner skill set is the ability to just kind of remain calm in this roller coaster of stress, right? you can try a few things, but if it's not gonna work, you don't, it's not maybe the main thing that you're looking at, like what the printers aren't working or whatever. That's not the biggest problem. The biggest problem is what are the ripple effects of this? Like why, how do I get these 1,000 people in? The keynote is paid to start in 10 minutes. How do they get in? So you just have to make like decisions, say, just go in.
Jen: Yeah.
Josh: Like we're not gonna badge you, just get in and go and attend that. And then after the keynote, get coffee and come back here and grab your badge. So from the attendee's point of view, they're like, no big deal.
Jen: Yep.
Josh: Right? They get to see what they want. They get to maybe have a shorter line anyway because they're distributed over a coffee break. And to them it's fine. But to us it's like the end of the world. And it's about how do we deal with those catastrophes with grace? and just deal with it.
Jen: So, I've been working a lot on translations this week, and that's one of the things that we've actually had to solve for is that if you can't print your badge. And so, what we have is we've got this email and it says emergency send only, right? And it sits there and it is ready to go. It has been proofed by the onsite team and everything, but it is a digital badge. And so, should everything go to heck in a handbasket, what we do is we can go and we can kick out this email out to our attendees, and then they get it on their phone, And because these are field marketing events, these are all going to be people that'll have— that should have their phones with them, right? They've got the internet connection through their cell provider and they're going to be able to go and pull up that email and then they can kind of continue on their way. So we can continue doing the scanning because our scanners are still going to work in offline mode. We just need to sync them at the end of the day, right? We can continue to run the event mostly as normal, even without our physical badges, which I think is pretty cool. And we actually had to invoke it at an event last year. Nobody was happy with us, but we were able to do it. We were able to successfully conclude the event and get all of our scan data. And I think that, particularly when you're talking about our exhibitors and our sponsors, right, and that we were doing training sessions and everything else, that is essential.
Josh: Yeah. And, and I would say one of the things is, it's kind of an offshoot to this, but when stuff like that happens, because it will happen, it always happens, Despite the best amount of planning and 20 steps ago you came up with 5 contingencies, it doesn't matter. Something will happen. And that's what makes this job stressful, but it also makes it wonderful. Like, I love that constant stress and change and solving and everything else. It's a lot of fun. It's also stressful for sure.
Jen: Yes.
Josh: But I think in the— you need that ability to say, to pause. and say, what is our best course forward and how will that affect the attendee experience? And a lot of times what we think is an emergency, the attendees don't even notice, to be quite honest. Right.
Jen: Yeah.
Josh: But in the moment, fault doesn't matter. That's not helpful. We just need a solution. In fact, even after when we're doing debriefs, I mean, unless it's gross negligence on somebody didn't do something. It's just an opportunity to like, let's learn from this, create some— how do we stop it from happening again next time? And let's move on and get better.
Jen: Yeah.
Josh: And I mean, I've been in cultures where we worked where I'd like, well, I sent Jen a Slack like a week ago, so it could be her fault, right? It doesn't matter, right?
Jen: No.
Josh: But I've seen people go into that mode of COVID your butt. We're all human. We all screw up all the time. And it's how we deal with those emergencies and the stress and the change. That's what sets us apart as good event planners.
Jen: Yeah.
Josh: And in fact, you know, some of the biggest enterprises that I've worked with, they will keep me on even if there's something that goes wrong because you own it, say, this is how we're gonna solve it. And it's how you deal with the problem, right?
Jen: Yeah.
Josh: And that's something that they respect and they would rather have somebody that, like teams that deal with problems head-on, fix them, and they know they can count on that.
Jen: Yeah. I, when I first started doing event technology, however many years ago, I came in and I was leading the teams right off the bat, knew nothing about events. And here I am in charge of a flagship event. So that was really fun. Talk about learning on the job. But what I told my team, because I had a team of people that knew what they were doing, I was like, you know what, we succeed or we fail as a team. Our attendees don't care whose fault it is because I was working with different vendor teams. I was pulling together like 6 different vendor teams. Our scanner scanning people were one team, the CMS was a different supplier, registration was another supplier, front end was another supplier, video was another supplier. Like nobody cares. All the attendee knows is that the keynote looks like crap and they don't care if the problem is the internet, they don't care if it's because the website's not loading the video correctly. Like all those things, it does not matter. So, we have to work together as a team to figure out how to solve it. And then, of course, we need to own up, right? But that also means that you develop this environment where you can have like the give-get, right? It's like, okay, like, I'm sorry that I had to do that, that that had to happen last time. You know, we got put under this pressure, so this change request came in. I appreciate the extra effort that you guys came in and like, okay, now you guys over here, it's time for you guys to step up. And we build this kind of give-get. sort of relationship so that nobody was constantly the one that was having to just give and give and give.
Josh: Yeah. And people who know me well, I have an expression I've used for forever, which is nobody's too good to carry a box.
Jen: Nope.
Josh: When you are on site at events, it doesn't matter what your job is. You could be the most fancy important person ever, but you're not too good to hang lanyards because in that moment, That is what is critical, um, to doing that. And yeah, you know, that's how we have to live when we're doing events for sure.
Jen: Yeah, like I've hung lanyards, I have put lanyards on badges, right? I'm down there to watch the mobile app, but I'm like, you know what, we have to go because our equipment didn't arrive. So we had to go and do a whole shopping thing and buy all the stuff from— we bought out like every office supply store in like a 10-mile radius to put together our badges for the next day. So we all stayed up like until midnight like trying to string these things together, and that's just what you do.
Josh: That's right, it's exactly what you do. It's great.
Jen: Yeah, well, Josh, I want to thank you so much. This has been a really fun conversation that has like tackled a ton of different topics, and I've really enjoyed this. And I love the fact that you and I share a very similar mindset toward tackling events, particularly on the event tech side of the house. And I'd love to give you a couple of minutes to tell my listeners today a little bit about you, your company, if you wish, anything else, how they can get in touch with you or Amego, and the platform is yours to close out.
Josh: Oh, the pressure. It's like my ShamWow moment. Um, so, uh, what do I do? So at Amego, I do, uh, AI solutions, which is sort of— I, I have sort of a dual role. Um, I drive internal innovation at Amego, um, where we're constantly developing and weaving AI into our solutions. And the other element is sort of partnering with enterprise clients to elevate the attendee experience sort of from pre-event to on-site, and how can we, you know, make it better for them and kind of work— I work directly with them on that. So that's kind of my hybrid role.
Jen: And Amigo does what? Amigo does what?
Josh: Amigo does what? I should maybe start there. So Amigo makes makes conference apps for attendees. And we do a lot of— we've sort of taken— we have a lot of people who have come from different big enterprises, and with that, they brought all the experience of what we're looking for. So I think we've got a really amazing offering for a conference app, and we're getting some fantastic enterprises coming over to us and doing some great work with us. Um, I think one of the really interesting things that we're doing right now with AI, so we'll stay on that topic, is we're— one of the ways we're weaving AI into our product is we've created a new, uh, element called Sidekick, which is— everybody seems to be putting chatbots into things, and this is not that. We are— um, this is very much a push technology, not a pull. So it is— it's sort of taking the 200 things that We plan for events and all these things we put all this thousands of hours into, but attendees only see 12 of those things, right? It's what's in front of them. So how do we unlock the event for people? And it's by taking presenting the right opportunity at the right time to the right attendees across everything sponsors, speakers, sessions, peer networking, all that kind of thing, and bringing it to their fingertips at the right moment and pushing it to them all in a very graphical. beautiful, feature-rich way. And I mean, it does chatbot operations as well, but that is so far down the list of what it is. But to me, that's— it's so exciting to be able to work in that and innovate with what's new, what can we make better in this AI delivering an event attendee experience to people.
Jen: That's really cool.
Josh: That's kind of what I'm doing and what Amego does. And and having a lot of fun doing it.
Jen: And how can my audience get in touch with you and/or Amego?
Josh: amego.com is A-M-E-G-O dot com. And I'm on LinkedIn, happy to talk to anybody at any time.
Jen: Yeah. OK, well, thank you so much, Josh. I look forward to chatting with you again soon.
Josh: Will do. Great to see you, Jen.
Jen: Yeah. Thanks for listening in to another roller coaster someone else rode so you don't have to. If you enjoyed this conversation, please take a moment to rate, review, subscribe, and share so other event pros can find the show. Until next time, tame the mayhem. Audiocracy.
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